Sodium Azide → Methyl 4-azido-2,3,5,6-tetrafluorobenzoate

HRID 750406Notes

Reaction equation

HRID 750406 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:16])[C:9]([F:17])=[C:8](F)[C:7]=1[F:19]>CC(C)=O.O>[N:1]([C:8]1[C:7]([F:19])=[C:6]([F:5])[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:16])[C:9]=1[F:17])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 606853Methyl Pentafluorobenzoate

Product 1

HCID 129750Methyl 4-azido-2,3,5,6-tetrafluorobenzoateYield 94.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

All reaction steps were carried out with protection from light due to the sensitive nature of the azido group. First, a mixture of NaN3 (300 mg, 4.6 mmol) and methyl pentafluorobenzoate (0.972 g, 4.3 mmol) in acetone (8 mL) and water (3 mL) was refluxed for 8 hours. The mixture was cooled, diluted with 10 mL of water, and then extracted with diethyl ether (3×10 mL). The extract was dried (anhydrous Na2SO4) and evaporated to give methyl 4-azido-2,3,5,6-tetrafluorobenzoate (1.01 g, 94%), as off-white flakes, mp 53.6-54.3° C.

Workup

  1. customAll reaction steps
  2. temperaturewas refluxed for 8 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with diethyl ether (3×10 mL)
  5. dry with materialThe extract was dried (anhydrous Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-4ac1bb4ba7984a7ea69cb67c523c2de6
Source dataset
uspto-grants-2008_07
Patent number
US07405034B2

Reaction notes

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